Potassium Iodide → 5-methoxy-3-[N-(4-(4-fluoro-phenyl)-butyl)-1,2,5,6-tetrahydro-pyridin-3-ylmethyl]-1H-indole

HRID 355997Notes

Reaction equation

HRID 355997 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]1[CH2:14][NH:15][CH2:16][CH2:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:28][CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]1[CH2:14][N:15]([CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=2)[CH2:16][CH2:17][CH:18]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 30168891-(4-Chlorobutyl)-4-fluorobenzeneHCID 189408175-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole

Product 1

HCID 189408305-methoxy-3-[N-(4-(4-fluoro-phenyl)-butyl)-1,2,5,6-tetrahydro-pyridin-3-ylmethyl]-1H-indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound of Description 5 [5-methoxy-3-(1,2,5,6-tetrahydro-pyridin-3-ylmethyl)-1H-indole] (1.4 g; 0.0058 mol), potassium carbonate (4 g; 0.0029 mol), a catalytic amount of potassium iodide (0.030 g) and compound of Description 9 [1-(4-chloro-butyl)-4-fluoro-benzene] (5.4 g; 0.029 mol) in dimethylformamide (40 ml) was heated at 80° C. for 6 hours. The reaction mixture was cool down to room temperature. quenched with water and then extracted with ethyl acetate. The organic extract was dried (MgSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5), the desired compound was obtained as an oil. A solution of this oil in methanol was saturated with gaseous hydrogen chloride. A solid was precipitated. The title compound hydrochloride was collected by filtration, washed with hexane and dried under vacuum (0.66 g).

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. customevaporated under vacuum
  6. customAfter purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol/ammonia (95/5/0,5)

Sources & evidence

ORD record
ord-4b065107e0e6472fbb63aedb1d7a3765
Source dataset
uspto-grants-1998_11
Patent number
US05834493

Reaction notes

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